Hi Jowel and welcome.
Number 1,2 &3 is, as Jacqui says, get to a club night and have a look through scopes.
And I reckon an 8" dob is probably the ideal start. They are quite portable and you can easiy move them with a trolley if you like. EQ mounts are much more complex and expensive and for $500 you would end up with not much scope to go with it.
But look through one. Be aware that although you will be able to see heaps through an 8" telescope, things will not appear as they do in astro images.
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